Ever since I helped create Urbanspoon I’ve had a penchant for building software that’s easy to use, mildly provocative and fun. Those ingredients are a potent combination when mixed in the right proportions.

My most recent project is PickHealthInsurance, which helps consumers pick a health insurance plan. I released the first version yesterday and it quickly shot up to #1 on Hacker News, my favorite startup news site. It turns out that self-employed people everywhere are having trouble picking insurance.

How did a lowly software engineer like me end up sticking my nose into the insurance business?

A few weeks ago I realized my COBRA was about to run out. I’ve purchased individual health insurance before so I wasn’t completely terrified, though my memories were unpleasant. I started poking around online and quickly became frustrated. There are only a few options for buying insurance online and I find them clunky and dated.

You have to plug in a fair bit of personal information before they start revealing rates and plans. Many of the most important details are squirreled away in hard to find places. For example, did you know that some plans that claim to cover maternity have a separate $20,000 deductible? Personally I want to know that kind of thing right up front before I apply for a plan.

I decided that I wanted to build my own health insurance picker. My background is in software engineering, though I can fake user interface design in a pinch. I had a few goals for PickHealthInsurance:

Explain confusing terms like “coinsurance” and point out the difference between a PPO and a POS

Show plan stats up front, not buried deep within the bowels of the application process

Make it easy to use and blazingly fast

The response so far has been overwhelmingly positive. People are very excited to see something innovative for health insurance. I had a hunch that I wasn’t the only one frustrated by the health insurance shopping process.

The release of PickHealthInsurance also kicked off a robust discussion about insurance pricing and lack of coverage. You can read some of the comments here.

Reading through some of the awful insurance experiences was an eye opener. I’d love to improve PickHealthInsurance and make it possible to compare the final quotes offered up by the plans, not just the advertised rates. That might take a few more weeks, though.

1. Any plans to add more UrbanSpoon like rating features? Seems like this is a natural, although it will doubtless be argued than health plans are not restaurants.

2. Can you tell us a little about the business model you’re planning on using here? Assuming you’ll be expecting some sort of fee from plans/brokers. If you go that route, do you think you’ll sacrifice consumer trust?

3. Curious for your take on the various healthcare rating sites out there. There are quite a few, but a lot of people aren’t so sure about their reliability. Is this something you’ve looked at?

Ratings – maybe. My experience at Urbanspoon tells me that many reviews are from boosters (restaurant owners) or haters (disgruntled employees / patrons). The middle ground is rare. I bet the situation is even worse with health care plans, since they are so divisive. A simple 1-5 stars type voting system might be possible, though.

Business model – no firm plans yet. I’ve always had good luck building a great product first and then layering on the business model later. After all, without site traffic there’s no business in any case!

The individual insurance market is expected to expand in 2014; however, from the recent numbers I have seen from eHealthinsurance, the individual market is suffering. Cigna is also pushing for more individual plan signups. With the individual mandate under threat, I am curious to what will happen in the individual market.

I am with you on the reviews. It is hard to review health insurance. I think the reviews should be more professional or you should employ a “matching” program. There really are not bad plans, just plans with more risk and plans built for different types of lifestyle. For me, I am 23 and get sick 3 times a year. I spend 200 bucks a month on premiums. Am I getting my money worth?

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